Natural product leads for drug discovery: Isolation, synthesis and biological evaluation of 6-cyano-5-methoxyindolo[2,3-a]carbazole based ligands as antibacterial agents

Songpo Guo; Suresh K. Tipparaju; Scott D. Pegan; Baojie Wan; Shunyan Mo; Jimmy Orjala; Andrew D. Mesecar; Scott G. Franzblau; Alan P. Kozikowski

doi:10.1016/j.bmc.2009.08.061

Natural product leads for drug discovery: Isolation, synthesis and biological evaluation of 6-cyano-5-methoxyindolo[2,3-a]carbazole based ligands as antibacterial agents

Songpo Guo, Suresh K. Tipparaju, Scott D. Pegan, Baojie Wan, Shunyan Mo, Jimmy Orjala, Andrew D. Mesecar, Scott G. Franzblau, Alan P. Kozikowski

Research output: Contribution to journal › Article › peer-review

Abstract

Indolo[2,3-a]carbazole based inhibitors were synthesized from readily available indigo via a seven-step linear synthetic sequence with a moderate overall yield. The inhibitors were selectively and readily functionalized at the nitrogen on the indole portion of the carbazole unit. The synthesized analogs displayed moderate inhibitory activities toward Bacillus anthracis and Mycobacterium tuberculosis, indicating that indolo[2,3-a]carbazoles could serve as promising leads in the development of new drugs to combat anthrax and tuberculosis infections.

Original language	English (US)
Pages (from-to)	7126-7130
Number of pages	5
Journal	Bioorganic and Medicinal Chemistry
Volume	17
Issue number	20
DOIs	https://doi.org/10.1016/j.bmc.2009.08.061
State	Published - Oct 15 2009
Externally published	Yes

Keywords

Anthrax
Carbazole
Tuberculosis

ASJC Scopus subject areas

Biochemistry
Molecular Medicine
Molecular Biology
Pharmaceutical Science
Drug Discovery
Clinical Biochemistry
Organic Chemistry

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10.1016/j.bmc.2009.08.061

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Guo, S., Tipparaju, S. K., Pegan, S. D., Wan, B., Mo, S., Orjala, J., Mesecar, A. D., Franzblau, S. G., & Kozikowski, A. P. (2009). Natural product leads for drug discovery: Isolation, synthesis and biological evaluation of 6-cyano-5-methoxyindolo[2,3-a]carbazole based ligands as antibacterial agents. Bioorganic and Medicinal Chemistry, 17(20), 7126-7130. https://doi.org/10.1016/j.bmc.2009.08.061

Natural product leads for drug discovery : Isolation, synthesis and biological evaluation of 6-cyano-5-methoxyindolo[2,3-a]carbazole based ligands as antibacterial agents. / Guo, Songpo; Tipparaju, Suresh K.; Pegan, Scott D.; Wan, Baojie; Mo, Shunyan; Orjala, Jimmy; Mesecar, Andrew D.; Franzblau, Scott G.; Kozikowski, Alan P.

In: Bioorganic and Medicinal Chemistry, Vol. 17, No. 20, 15.10.2009, p. 7126-7130.

Research output: Contribution to journal › Article › peer-review

Guo, S, Tipparaju, SK, Pegan, SD, Wan, B, Mo, S, Orjala, J, Mesecar, AD, Franzblau, SG & Kozikowski, AP 2009, 'Natural product leads for drug discovery: Isolation, synthesis and biological evaluation of 6-cyano-5-methoxyindolo[2,3-a]carbazole based ligands as antibacterial agents', Bioorganic and Medicinal Chemistry, vol. 17, no. 20, pp. 7126-7130. https://doi.org/10.1016/j.bmc.2009.08.061

Guo, Songpo ; Tipparaju, Suresh K. ; Pegan, Scott D. ; Wan, Baojie ; Mo, Shunyan ; Orjala, Jimmy ; Mesecar, Andrew D. ; Franzblau, Scott G. ; Kozikowski, Alan P. / Natural product leads for drug discovery : Isolation, synthesis and biological evaluation of 6-cyano-5-methoxyindolo[2,3-a]carbazole based ligands as antibacterial agents. In: Bioorganic and Medicinal Chemistry. 2009 ; Vol. 17, No. 20. pp. 7126-7130.

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title = "Natural product leads for drug discovery: Isolation, synthesis and biological evaluation of 6-cyano-5-methoxyindolo[2,3-a]carbazole based ligands as antibacterial agents",

abstract = "Indolo[2,3-a]carbazole based inhibitors were synthesized from readily available indigo via a seven-step linear synthetic sequence with a moderate overall yield. The inhibitors were selectively and readily functionalized at the nitrogen on the indole portion of the carbazole unit. The synthesized analogs displayed moderate inhibitory activities toward Bacillus anthracis and Mycobacterium tuberculosis, indicating that indolo[2,3-a]carbazoles could serve as promising leads in the development of new drugs to combat anthrax and tuberculosis infections.",

keywords = "Anthrax, Carbazole, Tuberculosis",

author = "Songpo Guo and Tipparaju, {Suresh K.} and Pegan, {Scott D.} and Baojie Wan and Shunyan Mo and Jimmy Orjala and Mesecar, {Andrew D.} and Franzblau, {Scott G.} and Kozikowski, {Alan P.}",

note = "Funding Information: This work was supported in part by DOD ( W81XWH-07-1-0445 ) and by NIH Grant ( 1R01GM075856 ).",

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doi = "10.1016/j.bmc.2009.08.061",

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AU - Guo, Songpo

AU - Tipparaju, Suresh K.

AU - Pegan, Scott D.

AU - Wan, Baojie

AU - Mo, Shunyan

AU - Orjala, Jimmy

AU - Mesecar, Andrew D.

AU - Franzblau, Scott G.

AU - Kozikowski, Alan P.

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N2 - Indolo[2,3-a]carbazole based inhibitors were synthesized from readily available indigo via a seven-step linear synthetic sequence with a moderate overall yield. The inhibitors were selectively and readily functionalized at the nitrogen on the indole portion of the carbazole unit. The synthesized analogs displayed moderate inhibitory activities toward Bacillus anthracis and Mycobacterium tuberculosis, indicating that indolo[2,3-a]carbazoles could serve as promising leads in the development of new drugs to combat anthrax and tuberculosis infections.

AB - Indolo[2,3-a]carbazole based inhibitors were synthesized from readily available indigo via a seven-step linear synthetic sequence with a moderate overall yield. The inhibitors were selectively and readily functionalized at the nitrogen on the indole portion of the carbazole unit. The synthesized analogs displayed moderate inhibitory activities toward Bacillus anthracis and Mycobacterium tuberculosis, indicating that indolo[2,3-a]carbazoles could serve as promising leads in the development of new drugs to combat anthrax and tuberculosis infections.

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KW - Carbazole

KW - Tuberculosis

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Natural product leads for drug discovery: Isolation, synthesis and biological evaluation of 6-cyano-5-methoxyindolo[2,3-a]carbazole based ligands as antibacterial agents

Abstract

Keywords

ASJC Scopus subject areas

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